


Like A Virgin

by thelonelywriter



Series: 30 Day OTP NSFW Challenge [24]
Category: Supernatural
Genre: 30 Day OTP Porn Challenge, Alternate Universe - Bar/Pub, Anal Fingering, Anal Sex, Bottom Castiel, Loss of Virginity, M/M, Plot What Plot, Porn Without Plot, Shameless Smut, Shy Castiel, Smut, Strangers to Lovers, Top Dean
Language: English
Status: Completed
Published: 2015-08-11
Updated: 2015-08-11
Packaged: 2018-04-14 02:49:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,939
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4547283
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>Once Dean and Cas had gotten into Dean's apartment, part of Dean expected Cas to slam him up against a wall, to ravish his mouth, because Dean knew that some pretty introverted people could be total sex freaks. The other part of him expected Castiel to be a tease, or to make it heated with slow, solid, and graceful movements. None of Dean expected Cas to look completely nervous with wide eyes. "Hey, you alright?" Dean asked hesitantly. Castiel plopped down on the couch, pinching the bridge of his nose.</p><p>"Dean, there's something I failed to mention about myself," he said, and Dean immediately panicked internally. What was Cas holding back? Cas bit his lip, then looked up at Dean. "I'm still a virgin," he sighed. Dean paused for a minute because there were a million things running through his mind.</p>
            </blockquote>





	Like A Virgin

**Author's Note:**

> Day Twenty Four was, 'Shy,' and do you SEE what i did with the title

All Dean wanted was a one night stand to loosen up a bit, to relieve some stress in his life. He figured maybe he’d find a younger guy with an amazing build, or maybe a really hot girl with great boobs. But, what he found was not exactly either of those two fantasies. 

Dean was standing at the bar, about to make his move on a petite little brunette, when he saw him out of the corner of his eye. He was this gorgeous guy with these chiseled cheekbones, and perfect, pale skin, cheeks slightly flushed as another older man crowded him, flashed him a smile that was downright predatory. Dean could tell that the guy who was shying away was uncomfortable, so he decided to take some action.

"Hey, babe, is there something wrong?" Dean asked as he sidled up next to the attractive, younger man. The taller man who had been crowding him backed off a bit, his eyes flickering between the two. 

"Oh, uh, I didn't know you two were together," the man said, beginning to back away. Dean smiled, and nodded surely. "Sorry," he mumbled, turning to walk away as Dean sat across from the attractive, mystery man.

"Thanks, you know, for that," he said softly, holding out his hand. "My name is Castiel," he told Dean as they shook hands. Dean smiled at the name before pulling his hand away.

"Dean," Dean simply told him. “I like that name, Castiel,” he complimented, and Castiel smiled softly.

“Thank you. Not many people appreciate it,” he sighed.

“Well, they should appreciate it more,” Dean said kindly. 

There was a moment of soft silence before Dean spoke. “So you’re alright, that guy didn’t hurt you or anything?” he clarified, and Castiel shook his head.

“Embarrassingly enough, that happens to me often. I usually don’t have someone like you to come in to rescue me though,” he said, looking up at Dean. Dean’s spine tingled with all the warmth that was held behind those kind eyes.

“Well that’s too bad, you deserve to be saved more often,” Dean murmured, holding his gaze with Cas’. Castiel blushed, looking away.

“You’re very kind to me,” he stated. Dean simply smiled, not making any handsy moves or dumb pick up lines, just holding a conversation with a sweet guy.

“Should I take that as a compliment or a statement?” Dean teased, and Castiel chuckled, and the sound was music to Dean’s ears, drowning out all the other noises at the loud bar.

“I guess both,” Castiel responded with a grin. “Mostly the first part, however,” he continued. Dean smiled wide back at him. This guy was definitely a keeper.

\---

After a few soft touches and longing glances, Dean finally took the initiative to ask Castiel back to his apartment. By the time they had gotten there, they were both barely even buzzed, and Castiel was coming out of his shell, laughing at all of Dean’s dumb jokes, reciprocating conversation with ease, and smiling wide nearly the whole time.

Once Dean and Cas had gotten into Dean's apartment, part of Dean expected Cas to slam him up against a wall, to ravish his mouth, because Dean knew that some pretty introverted people could be total sex freaks. The other part of him expected Castiel to be a tease, or to make it heated with slow, solid, and graceful movements. None of Dean expected Cas to look completely nervous with wide eyes. "Hey, you alright?" Dean asked hesitantly. Castiel plopped down on the couch, pinching the bridge of his nose.

"Dean, there's something I failed to mention about myself," he said, and Dean immediately panicked internally. What was Cas holding back? Cas bit his lip, then looked up at Dean. "I'm still a virgin," he sighed. Dean paused for a minute because there were a million things running through his mind. 

"So that's why you're so nervous," Dean stated, and Castiel nodded, standing up to move closer to Dean.

"Dean, listen, I completely understand if you want someone more experienced, it's my fault that I didn't tell you," he apologized. 

"Cas, it's not that, it's... you should do it with someone special, Cas, I'm just some random guy," Dean told him, though it pained him to say it. He couldn't quite explain it, but he felt like there was more to it, more between them. Castiel took a deep breath, and stepped up to Dean, looking him in the eyes. He placed a hand on his shoulder, and smiled softly.

"You're different, Dean. I can tell," he said quietly before his hand moved up to cup the back of Dean's neck. Then, as if in slow motion, Dean was bringing his lips down, watching Castiel's eyes flutter shut right before his own did, right before the softest of lips met his his own, and both their breaths hitched slightly at the sweet contact between them.

The kiss was chaste and slow before Dean pulled away slightly, bringing his hand up to cup one side of Castiel's face. "Cas, are you sure?" Dean murmured against his lips. Castiel smiled, and kissed him a little harder. 

"Dean, I can assure you that as long as you're willing to deal with a stammering, nervous, thirty year old virgin that you didn't bargain for, I will gladly let you take my virginity," Castiel said softly, holding eye contact with Dean. Dean smiled, then pulled him closer, placing his other hand on Castiel's hip.

"I'm gonna take good care of you, Cas, promise," Dean murmured before he brought his lips back to Castiel's.

Dean let Castiel control the speed of the delicate kiss as one of his hands came up behind Dean's neck to connect with the other one. Castiel finally parted his lips, beckoning Dean's tongue in shyly. Dean took it slow, mapping Castiel's mouth, and feeling Castiel's tongue slide against his own.

Castiel let out a pleased sigh at the feeling of Dean, Dean who he barely knew, but felt like he had known a lifetime. Castiel knew that it was cliché and most likely stupid, but it just felt _right_. And who was he to deny himself that?

Castiel timidly pressed his body into Dean’s, relishing in the warmth it offered as Dean laid a reassuring hand on the small of his back. Dean pulled away only ever so slightly to ghost his lips over Cas’ jaw, feeling the slight stubble there. He moved downwards, listening to Castiel’s breathing pick up faintly as Dean pressed kisses to his skin, scraping his teeth across it and nipping gently. His hand moved upwards on Castiel’s back, running his hand over his shoulder blades. Castiel’s hands ran through Dean’s hair as he took a shaky breath. “We can move this to the bedroom if you’d like,” Dean murmured into his skin. “But if you wanna keep doing this, or you wanna stop, you tell me, okay?” Dean told him, and Castiel nodded, tugging Dean a little closer.

“We can go to the bedroom,” he said quietly, and Dean smiled, giving him a sweet kiss. He interlaced their fingers, guiding him to the bedroom, peppering him with sweet kisses as they went.

Dean wrapped Castiel up in his arms, and Castiel couldn’t help but let out a little giggle as Dean smiled wide and kissed him, laying him gently down on the bed. Dean laid down next to him, making sure not to crowd him as he slotted one leg between Cas’, and propped himself up on one elbow, his other hand stroking over Castiel’s waist. He could feel Castiel hard against his leg, and it wasn’t long before Castiel was trying to hold his hips back from rutting up against Dean. Dean could tell, and nipped at Castiel’s ear. “It’s okay baby, I don’t mind,” Dean whispered, and the gruff voice sent shivers down Castiel’s spine.

Castiel groaned quietly as he let his hips roll forwards, and he bit his lip at the friction. “You wanna take this off yet?” Dean asked, tugging at Castiel’s shirt. Castiel nodded eagerly, and Dean shifted them, helping him pull it off. Castiel then toyed with the hem of Dean’s shirt, looking up at Dean with silently questioning eyes. Dean smiled and gave him a kiss before pulling off his own shirt, and throwing it aside, the two left in only their jeans.

Castiel rolled onto his back, tugging Dean with him, connected by the lips as the two smiled into the kiss, and Dean straddled him. Dean began to move his kisses lower and lower until he paused, experimentally brushing a thumb over one of Castiel’s nipples. Cas immediately gasped, his hips bucking upwards into Dean’s. Dean smiled, then circled the hardened peak with his fingers, pinching and tweaking before he leaned down, mouthing over it until Castiel was a mess, his hair out of place, his chest and face flushed the prettiest of pink. “Fuck, Dean,” Castiel choked out as Dean moved onto the next one, and Castiel’s hands threaded through Dean’s hair as his hips bucked upwards, desperately grinding into Dean’s. 

Dean pulled away to look at Cas with a sly grin, then placed a hand on his hip. “I’m guessing you wanna keep going?” Dean said, though, by the state of Castiel, he already knew the answer. Castiel nodded furiously, and Dean moved forward to kiss him. Dean slipped one finger into Castiel’s jeans, and Castiel opened his eyes to be met with Dean’s green ones. “You okay if these come off?” Dean asked softly, and Castiel blushed a bit but nodded. Dean shimmied down Castiel’s body before looking up at him. “Boxers too?” he inquired. Castiel bit his lip and nodded shyly, and Dean helped him wiggle out of them, throwing them aside.

Dean was met with the sight of Cas’ already leaking, already hard cock. But he didn’t go straight for it, he smoothed his hands over the lean muscle of Castiel’s thighs that were quivering faintly. “You okay?” Dean asked, looking down at Cas, who was chewing on his lip.

“I’m just a little nervous,” he said quietly. 

“Hey, it’s okay, I’m not gonna hurt you, Cas. If you wanna stop, just tell me, and don’t be afraid to let me know if you wanna take things slower. Does that sound good?” Dean asked, and Castiel smiled, nodding. Dean leaned down, pressing soft kisses to Castiel’s inner thighs, rubbing circles with his thumbs to relax the tense muscle. Soon enough, Castiel was pliant beneath Dean, his eyes shut, his lips parted slightly in contentment. It was only then when Dean brought a hand up to Castiel’s cock, wrapping a loose fist around it, and stroking it once. 

Castiel sucked in a breath of air, then followed it with a quiet, shaky moan once Dean gave it a second stroke. Dean gave it a couple strokes before he brought his other hand down, tentatively stroking over Castiel's balls, sneaking one finger back to find the furl of muscle he was looking for. Castiel shuddered underneath him, and Dean kissed the inside of his thigh in recognition. "Is it okay if I keep going?" Dean asked softly, and Castiel gave a timid nod. Dean rose from the bed, and Castiel furrowed his eyebrows. "I'm just getting some lube, baby, don't worry," he reassured as he walked to his bedside table, rummaging for the lube and a condom packet. 

Once Dean got back on the bed, he smoothed his hands over the outside of Castiel's thighs before cradling the undersides of his knees. "You wanna lift these to your chest for me?" Dean asked, and Castiel nodded, doing so slowly. Dean scooched a bit closer, and kissed Cas sweetly. "You're doing so beautiful for me, Cas," he encouraged. Castiel smiled at the praise, and watched with anticipation as Dean opened the lube and poured a generous amount onto one finger. "This is gonna be a little cold at first, but just relax, okay?" Dean instructed, and Castiel let out a breath of air, nodding. 

Dean gently pressed his finger to Castiel's rim, swirling his finger in circles to warm up the lube, and in hopes of relaxing Castiel. Sure enough, it worked, and he was slipping in one finger slowly until it was all the way in. He realized that the feeling must be strange to Cas, so he brought a hand up, grasping Cas' dick and softly stroking it, making Castiel sigh shakily.

He took his time, letting Castiel adjust as he watched all his ministrations with rapture. When he slipped in a second finger, Cas didn't even notice, as he was simply getting used to the feeling. Then he jumped slightly, gasping as sparks of pleasure shot through him when Dean hit that certain spot he had been looking for. "That okay?" Dean asked, and Castiel nodded furiously.

"D- do it again," he said, and Dean brushed his fingers over Castiel's prostate once more, and this time Castiel rocked his hips into it experimentally. "Oh, fuck," he cursed as Dean made a pleasurable routine, crooking his fingers in just the right way so that he was passing over his prostate, then hooking his fingers around Cas' rim before pushing them back in.

Dean kissed and nipped at the sensitive skin of Castiel’s thighs as his other hand worked loosely over Castiel’s cock. He added a third finger slowly and carefully, listening to the noises of pleasure Castiel was making beneath him. It was nearly all too much for Castiel, who could feel his nerves flying in all different directions at all the feelings and sensations that were shooting through him. Cas bit his lip, and shut his eyes tight, simply focusing on the feelings of Dean, Dean who was comforting him, not rushing him, letting Cas say when he wanted what. And Castiel decided then, that he was ready.

“I’m ready,” he told Dean, who slowed his movements.

“You sure?” Dean questioned, and Castiel opened his eyes, looking into Dean’s and nodding. Dean slowly pulled his fingers out, and momentarily shifted away, giving Castiel one last kiss before he took the condom packet in his hands.

What felt like an eternity later, Dean was positioned against Castiel. Dean gave him a look, and like a silent language Castiel nodded, taking a deep breath as Dean pushed in slowly, letting Castiel adjust to every inch until there was nothing more. Castiel controlled his breathing, getting used to the feeling, wiggling around a bit as Dean fought the urge to slam straight into Cas. “Move,” Castiel said quietly after a moment. Dean gave a slow and steady roll of his hips, and Castiel nodded, letting Dean keep going. Dean kept a slow pace, and at first, the feeling was strange to Cas, but then, he got used to it, and soon enough his eyes were fluttering shut, his head tipped back, revealing the pale skin on his neck that Dean was eager to kiss and lick. 

Dean smoothed over all the parts of Cas, his waist, his thighs, his back, and listened to Castiel as he started to moan in pleasure, as soft groans escaped his lips. Then, a certain thrust bleed into a long, desperate moan from Castiel. “Fuck, Dean, right there, oh my God,” he panted, shoving his hips into Dean’s. Dean made sure to angle his thrusts that exact way as his kissed down Castiel’s jaw.

“Fuck, you’re so damn beautiful,” Dean murmured into his skin as Castiel brought his hands up to Dean’s back, pulling him closer.

“Harder,” Castiel groaned in response. Dean gladly thrust faster and harder until Castiel was a mess underneath him, clawing at his back, and moaning loud enough so that Dean was sure he’s get some noise complaints from his neighbors the next morning.

“Dean,” Castiel keened as he felt his orgasm approaching quickly. 

“Shh, I got you, Cas,” he soothed as Castiel let out a long moan. Dean then realized that Cas’ cock had barely been touched, so he slipped a hand between them, knowing that Castiel would likely be pushed over the edge if Dean gave his dick a few strokes. Dean, in fact, was right, and Castiel soon felt hot come spurt between the two, his arousal burning bright inside of him as he arched off the bed with a breathless moan.

Dean groaned as Castiel went boneless beneath him, breathing heavily. Dean desperately thrust faster, chasing after an orgasm he was right on the edge off. Before he knew it he was coming with Castiel’s name on his lips as he tensed, then went limp, collapsing on top of Cas who was looking sated and happy.

Dean pulled out, his limbs still tangled with Castiel’s. He kissed lazily over Castiel’s skin, then smiled, and huffed a breath of laughter. “Pretty good for a virgin,” he whispered, looking up to Cas. Castiel nudged him with a smile.

Simply sitting there, the two breathed, listening to the soft sounds of the others breath. “Cas?” Dean said quietly.

“Yeah?”

“Do you wanna go out on a date with me, maybe, you know, sometime?” Dean asked. Castiel grinned widely.

“I’d be a fool to say no to someone like you, Dean,” Castiel responded, and Dean smiled up at him.

“You know, with one night stands I usually don’t let them stay overnight, but if you want then you’re welcome to. I have a feeling that you aren’t just a one night stand,” Dean told him softly. Castiel stroked a soft hand over Dean’s cheek.

“I get the same feeling.”

**Author's Note:**

> six more fics and we're golden, guys!! so let me know what you thought and what you disliked or liked, and what you'd like to see in the future!! and, as always, [my tumblr](http://blueyesintheimpala.tumblr.com/) :)


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